Patent GB-1261007-A (GB)
Title: Imidazolidinone derivatives
IPC: C07D295/088
Filed: 1970-03-26
Abstract: 1,261,007. Dibenzazepine derivatives. J. R. GEIGY A.G. 26 March, 1970 [28 March, 1969; 21 May, 1969], No. 14637/70. Heading C2C. Novel compounds of Formula I (in which X is H or Cl, m is 2 or 3, R 1  is methyl or ethyl, each of R 2  and R 3  is H or R 2  and R 3  together represent an additional bond) and their acid addition salts, are prepared by (a) reacting a reactive ester of a compound of Formula II with a compound of Formula III or an alkali metal derivative thereof, or (b) reacting a compound of Formula IV or an alkali metal derivative thereof, with a reactive ester of a compound of Formula V or (c) reacting a reactive ester of a compound of Formula VI with a compound of Formula VII in the presence of a basic condensation agent, or (d) reacting a compound of Formula III or an alkali metal derivative thereof, with a compound of Formula VIII  (in which Y is halogen) or an alkali metal derivative thereof, and, if desired, converting a resulting free base into an acid addition salt thereof. 5 - [2 - Methyl - 3 - (1 - piperazinyl) - propyl]- 10,11-dihydro-5H-dibenz[b,f]azepine is prepared by reacting 10,11-dihydro-5H-dibenz[b,f]azepine with 1-(3-chloro-2-methyl-propyl)-4-methyl piperazine to form 5-[2-methyl-3-(4-methyl-1- piperazinyl) - propyl] - 10,11 - dihydro - 5H- dibenz[b,f]-azepine, reacting this compound with cyanogen bromide to form 4-[3-(10,11-dihydro- 5H - dibenz[b,f]azepin-5-yl) - 2 - methyl - propyl]- piperazine-1-carbonitrile and simultaneously hydrolysing and decarboxylating this compound by treatment with hydrochloric acid. The corresponding 3-chloro compound is prepared analogously. 5 - [2 - Methyl - 3 - (1 - piperazinyl) - propyl]- 5H-dibenz[b,f]azepine is prepared by reacting 5- (3 - chloro - 2 - methyl - propyl) - 5H - dibenz- [b,f]azepine with 1-piperazine carboxylic acid ethyl ester to give 4-[3-(5H-dibenz[b,f]azepine-5- yl)-2-methyl-propyl]-piperazine-1-carboxylic acid ethyl ester and simultaneously hydrolysing and decarboxylating this compound by treatment with potassium hydroxide. Compounds of Formula VI and their esters are prepared by reacting #,4-dimethyl-piperazine-1- propanol with acetic anhydride to give 1-(2- methyl-3-acetoxypropyl)-4-methylpiperazine, reacting this compound with cyanogen bromide to form 4-(2-methyl-3-acetoxypropyl)-1-piperazine carbonitrile, hydrolysing arid simultaneously decarboxylating this compound by treatment with hydrochloric acid to give #-methyl-piperazine-1- propanol, reacting this compound with a 1- (haloalkyl)-3-R 1 -2-imidazolidinone and esterifying the resulting compound VI, e.g. by treatment with thionyl chloride or tosyl chloride. 1-(3-Chloropropyl)-3-ethyl-2-imidazolidinone is prepared by reacting 3-ethyl-2-oxazolidinone with (3-chloropropyl)-isocyanate. Compounds of Formula VIII are prepared by reacting diethanolamine with a 1-R 1 -isocyanate to form a 1-R 1 -3,3-bis-(2-hydroxyethyl)-urea and halogenating this compound, e.g. by treatment with thionyl chloride.  Pharmaceutical compositions for oral, rectal or parenteral administration comprise a compound of Formula I or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutical carrier. The compositions are useful in the treatment of psychosomatic disturbances.